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Dear Head Pro,

I'm just going to jump right into it. So I've been dating this pro for a few weeks now- he's great, and everything I'd want in a guy- graduated from an Ivy, works in finance now, takes me out on nice dates, etc. But I have two problems – First, I'm moving away in a month to start grad school, so I know this can't really go anywhere.  He knows this, and hasn't changed our relationship from dating to casual hook ups which I think is great.  The second problem is that I'm a virgin. I'm 23- but not a religious freak or anything- just didn't click with any other guys I dated.  I'm really into this pro though, and do want to lose it to him before I leave (because lets be real- the chances of us continuing to date after I leave are slim to none).  Is this a bad idea?  And how do I approach telling him that I still haven't swiped my v-card?


Virgin Betch

Dear Virgin Betch,

Cool, this again. So at the tender age of 23, you’ve finally found a guy you’ve decided is worthy of occupying vag street, and you’re asking me if it’s a bad idea? I think you’ve more or less answered your own question, seeing as how you said you “do want to lose it to him before you leave”. I guess if by bad idea you mean losing it to someone you’ll soon no longer be in contact with, I don’t see why it has to be. If anything, it probably beats losing it in highschool or college where you and the guy get stuck way up each others asses, leading to serious misconceptions as to what constitutes love followed by years of heartache and issues. If I’ve seen it once, I’ve seen it a thousand times.

As for telling him that you’re a virgin, it’s probably easier being older and out of college. He won’t be terrified of you turning into a clinger, both because you’re leaving soon and also because he’s a grown ass man who hopefully wouldn’t put up with unnecessary drama. I don’t think though, at this point, it’s some big conversation you need to have way in advance. It’s still a big deal for you, of course, but you are a tad late to the party. It’s like when someone in their 40’s finally gets their GED. Good for them, but no one’s throwing them a fucking party for it.

I’d wait for an evening when you’re feeling particularly saucy (and maybe just a little sauced) and use it as a conversational bridge between wherever you are at the moment and poundtown. Maybe in a restaurant if the talk turns sexual, get a little flirty and say something like “you know something I’ve never done…?” Sounds corny, but keeping things playful is the way to go to keep you in the mood and him from feeling too awkward.

If that doesn’t work, call him a pussy and make fun of him for not having tried to fuck you yet. Some guys get off on that stuff.

Congratulations on Becoming a Woman,

Head Pro

Dear Head Pro,

I'll skip the usual obligatory dick sucking, obviously I value your advice, otherwise I would not be asking for it.

I have a major dilemma on my hands and I'm in dire need of assistance. I have been friends with this pro, let's call him “jimmy”, for a few years now. I know that pro's and betches aren't normally friends and I have a strong feeling that he likes me. We text constantly and everyday, hang out regularly and whens he's drunk he tells me how much he loves me. Am I totally delusional or am I correct in saying that not many pros put that much effort into their friendships, let alone those with girls.

We've hooked up once and he knows I like him. He says he doesn't want a gf and that he's no good for me but didn't deny liking me back. Honestly I think he's in denial. He's a womaniser but always treats me with the utmost respect and recently has stopped hooking up with other girls which he has made of point of mentioning.

Although we are quite flirty, there is always a physical distance between us almost as though we're too scared to touch. Is this a sign of sexual tension? That he's not into me? Or thinks I'm cold?

I'm usually pretty level headed but I've lost my usual cool and I need advice on where you think my current situation stands and how I should progress from here. I think I really like him but also he's totally gorgeous and I want to fuck him. Any help would be much appreciated.

Many thanks,

Delusional Dater Phobe

Dear Delusional Dater Phobe,

I’m a little confused. You’ve hooked up before. He knows you like him. He claims that he’s stopped hooking up with other girls, and yet he doesn’t try to hook up with you. Other than drunkenly expressing his love for you (which is pretty common for bros), what does he do to make you think he likes you? Does he touch you? Does he get jealous of other guys? Does he stand outside your bedroom window, masturbating angrily yet passionately? Because that’s what I do that would be a little much.

Having a physical distance between you that neither one of you is willing to breach isn’t sexual tension – it’s the exact opposite. Sexual tension is when you’re afraid to be around each other because you’re afraid you won’t be able to keep your hands off one another. I know this because every woman I approach tries to distance herself from me as fast as she can, and the only reason I can think of is because if she didn’t she couldn’t help but start giving me mouth hugs right there on the spot. So if he’s being flirty but keeping his distance, not only might there not be any sexual tension, but he might not want to fuck you at all.

I don’t want a girlfriend right now” and “I’m no good for you” are two of bro’s most powerful tools for getting rid of a girl we’re just kind of over. On the other hand, I believe you when you say you spend a lot of time with/talking to each other, and saying he’s stopped hooking up with other girls is perplexing. I think what you have on your hands is one very confused bro.

This is kind of an ugly thing to say, but with nothing more to go on it sounds like this bro likes you but doesn’t find you attractive, or at least not attractive enough. I’m not making any assumptions about your looks, but it happens to bros all the time when we encounter girls who are awesome, but for whatever reason don’t give us itchy britches. Sure, we might feel a really deep appreciation for you, even love, and we might even give in and hook up with you under the right circumstances. But for whatever reason, be it perceived peer pressure or some very specific personal tastes, we just don’t see you quite in that way.

I can’t be sure, but that sounds like what you have on your hands. If you’re that close, maybe suck it up and put a move on him and see what happens. You might not like the result, but any result is better than no result.

You can't skip it if it's obligatory,

Head Pro

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